This article examines inclusivity in digital youth work initiatives which use and discuss media and technology. The research focusses on initiatives aimed at socially vulnerable youth. Socially vulnerable and digitally excluded youth face educational inequalities due to limited resources, such as inadequate hardware or lack of academic support at home (Correa et al., 2020; Faure et al., 2022; Garmendia & Karrera, 2019). Youth work as non-formal learning plays a crucial role here, possessing certain advantages that formal education does not have—for instance, the freedom to set needs-specific learning goals that are more responsive to societal signals. Through a two-fold comparative case study analysis, we delve deeper into the successful approaches to organising digitally inclusive digital youth work. The case studies (<em>N</em> = 14), located in Flanders, Belgium, were conducted through an in-depth analysis consisting of a QuickScan of practices and in-depth interviews with practice representatives. Our findings identify four success factors for the setup of digitally inclusive practices: (a) providing young people with the means to actively participate during the activity, (b) informing youth workers about digital inclusion factors, (c) providing youth workers with the means to seek help from other actors working on digital inclusion, and (c) including the target group in the creation process of the activity. Based on these four success factors, this study emphasises the importance of a signal-based approach that starts from the needs and talents of youth.